Role overview

Caseware is a long-established Canadian fintech company serving the global audit and accounting software market, with over 500,000 users across 130 countries. As Technical Program Manager for AI Programs, you will lead the planning, coordination, and execution of AI initiatives across the company’s product and solution portfolios, creating a unified view of AI work and ensuring consistent progress from strategic conception through market launch.

Key responsibilities

Manage end-to-end delivery of AI launch programs in collaboration with product, engineering, design, and go-to-market teams.
Identify and resolve cross-functional dependencies before they obstruct program progress.
Establish and maintain a single source of truth for tracking all AI initiatives across the organization.
Provide leadership with current, clear visibility into the status and trajectory of each AI program.
Act as a consistent unblocking force that keeps AI programs moving forward through all development stages.
Transform fragmented AI work into organized, predictable delivery processes.

Requirements

Strong technical fluency with the ability to communicate effectively with engineering and product teams.
Demonstrated experience managing complex, cross-functional programs at scale.
Proven ability to track, coordinate, and unblock multiple interdependent initiatives.
Experience providing stakeholders and leadership with clear program visibility and status reporting.
Capability to work in a fast-moving environment with high-visibility, strategic AI initiatives.

What makes this role worth considering

This is a newly created position offering the opportunity to shape how a category leader in assurance software develops and delivers AI capabilities. Based in downtown Toronto with hybrid flexibility (three days per week in office), you will work at the center of Caseware’s AI strategy, directly influencing how the company serves its global base of accounting and audit professionals.